Enantio- &amp; chemo-selective preparation of enantiomerically enriched aliphatic nitro alcohols using Candida parapsilosis ATCC 7330

Venkataraman, Sowmyalakshmi; Chadha, Anju

doi:10.1039/c5ra13593a

Cited by 12 publications

(4 citation statements)

References 67 publications

(82 reference statements)

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“…Even though cells harvested at 14 h produced the same ketone at less conversion (38%), these cells were used to visualise the site of biotransformation. For several other substrates reported earlier from our lab, the 14 h harvested cells produced the desired optically pure products with maximum ee (up to >99%) 1 2 3 6 7 26 29 30 33 34 35 .…”

Section: Resultsmentioning

confidence: 69%

Direct observation of redox reactions in Candida parapsilosis ATCC 7330 by Confocal microscopic studies

Venkataraman

Narayan

Chadha

2016

Sci Rep

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Confocal microscopic studies with the resting cells of yeast, Candida parapsilosis ATCC 7330, a reportedly versatile biocatalyst for redox enzyme mediated preparation of optically pure secondary alcohols in high optical purities [enantiomeric excess (ee) up to >99%] and yields, revealed that the yeast cells had large vacuoles under the experimental conditions studied where the redox reaction takes place. A novel fluorescence method was developed using 1-(6-methoxynaphthalen-2-yl)ethanol to track the site of biotransformation within the cells. This alcohol, itself non-fluorescent, gets oxidized to produce a fluorescent ketone, 1-(6-methoxynaphthalen-2-yl)ethanone. Kinetic studies showed that the reaction occurs spontaneously and the products get released out of the cells in less time [5 mins]. The biotransformation was validated using HPLC.

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Section: Resultsmentioning

confidence: 69%

Direct observation of redox reactions in Candida parapsilosis ATCC 7330 by Confocal microscopic studies

Venkataraman

Narayan

Chadha

2016

Sci Rep

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“…Lipase, esterase, halohydrin dehalogenase, and HNL catalyzed retro-Henry reaction are used in the kinetic resolution of a racemic β-nitroalcohol or an epoxide. [12][13][14][15][16] Alcohol dehydrogenase catalyzed asymmetric reduction, [17][18][19][20] and HNL catalyzed nitroaldol reaction [21][22][23][24][25] are the other two routes. Both kinetic resolution and asymmetric reduction requires an additional step of substrate preparation, while the former could provide a maximum 50% theoretical yield.…”

Section: Introductionmentioning

confidence: 99%

One‐Pot Enzyme Cascade Catalyzed Asymmetrization of Primary Alcohols: Synthesis of Enantiocomplementary Chiral β‐Nitroalcohols

2021

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Biocatalytic asymmetrization of inexpensive and stable primary alcohols to prepare enantioenriched β-nitroalcohols is an important development in green chemistry for the production of chiral pharmaceutical intermediates. Herein, we report a one-pot, two-step cascade reaction sequence in which first benzylic alcohols were oxidized to produce corresponding benzaldehydes using horse liver alcohol dehydrogenase (HLADH). The in situ generated aldehydes were then reacted in a biphasic medium with nitromethane by Arabidopsis thaliana hydroxynitrile lyase (AtHNL) or Baliospermum montanum HNL (BmHNL) catalyzed Henry reaction to produce stereoselective β-nitroalcohols with (R) or (S) configuration, respectively. Using HLADH-AtHNL, (R)-β-nitroalcohols were obtained in up to 64% conversion, and HLADH-BmHNL, (S)-β-nitroalcohols in up to 70% conversion, while in both cases excellent stereoselectivity (up to > 99% ee) was achieved. The concept was proven by functionalization of sp 3 CÀ H bond of ten simple achiral benzylic alcohols to enantiocomplementary chiral β-nitroalcohols.

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“…In 2008, Kroutil et al [25] reported on the conversion of 1-nitro-3-phenylpropan-2-one and 1-nitro-2-octanone into the enantiopure (S)-nitroalcohols in 47% and 75% yield, respectively, by using the lyophilized cells of Comomonas testoteroni. Recently [26], the whole cells of Candida parapsilosis ATCC 7330 were employed to catalyse the enantioselective reduction of some aliphatic derivatives 3 (only R = alkyl) in water with ethanol as a cosolvent, at room temperature, and in 4 h reaction time (conversion yields 54-76%, ee = 8.2-81%). The formation of the (R) or (S) enantiomer of the corresponding nitroalcohol depended upon the nature of the R group.…”

Section: Synthesis Of Nitroketones 3 and Biocatalysed Reduction To Dementioning

confidence: 99%

Biocatalytic Approach to Chiral β-Nitroalcohols by Enantioselective Alcohol Dehydrogenase-Mediated Reduction of α-Nitroketones

et al. 2018

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Chiral β-nitroalcohols are important building blocks in organic chemistry. The synthetic approach that is based on the enzyme-mediated reduction of α-nitroketones has been scarcely considered. In this work, the use of commercial alcohol dehydrogenases (ADHs) for the reduction of aromatic and aliphatic nitroketones is investigated. High conversions and enantioselectivities can be achieved with two specific ADHs, affording either the (S) or (R)-enantiomer of the corresponding nitroalcohols. The reaction conditions are carefully tuned to preserve the stability of the reduced product, and to avoid the hydrolytic degradation of the starting substrate. The further manipulation of the enantioenriched nitroalcohols into Boc-protected amminoalcohols is also described.

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Enantio- & chemo-selective preparation of enantiomerically enriched aliphatic nitro alcohols using Candida parapsilosis ATCC 7330

Abstract: The title biocatalyst mediates the asymmetric, chemoselective reduction of nitroketones wherein the keto group is preferred with respect to the nitro group.

Cited by 12 publications

References 67 publications

Direct observation of redox reactions in Candida parapsilosis ATCC 7330 by Confocal microscopic studies

Direct observation of redox reactions in Candida parapsilosis ATCC 7330 by Confocal microscopic studies

One‐Pot Enzyme Cascade Catalyzed Asymmetrization of Primary Alcohols: Synthesis of Enantiocomplementary Chiral β‐Nitroalcohols

Biocatalytic Approach to Chiral β-Nitroalcohols by Enantioselective Alcohol Dehydrogenase-Mediated Reduction of α-Nitroketones

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